1,2,3,8-tetrahydrobenzo[a]pyrrolo[4,3-c]carbazole-1,3-dione

ID: ALA421087

Chembl Id: CHEMBL421087

PubChem CID: 11161961

Max Phase: Preclinical

Molecular Formula: C18H10N2O2

Molecular Weight: 286.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1NC(=O)c2c1c1ccccc1c1[nH]c3ccccc3c21

Standard InChI:  InChI=1S/C18H10N2O2/c21-17-14-9-5-1-2-6-10(9)16-13(15(14)18(22)20-17)11-7-3-4-8-12(11)19-16/h1-8,19H,(H,20,21,22)

Standard InChI Key:  IUWAGZUDXHNNFN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA421087

   benzo(a)pyrrolo(3,4-c)carbazole-1,3(2H,8H)-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 286.29

Molecular Weight (Monoisotopic): 286.0742

AlogP: 3.36

#Rotatable Bonds: ┄

Polar Surface Area: 61.96

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.11

CX Basic pKa: ┄

CX LogP: 2.80

CX LogD: 2.72

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.49

Np Likeness Score: 0.47

References

1. Sanchez-Martinez C, Shih C, Faul MM, Zhu G, Paal M, Somoza C, Li T, Kumrich CA, Winneroski LL, Xun Z, Brooks HB, Patel BK, Schultz RM, DeHahn TB, Spencer CD, Watkins SA, Considine E, Dempsey JA, Ogg CA, Campbell RM, Anderson BA, Wagner J..  (2003)  Aryl[a]pyrrolo[3,4-c]carbazoles as selective cyclin D1-CDK4 inhibitors.,  13  (21): [PMID:14552791] [10.1016/s0960-894x(03)00791-1]

2. Routier S, Mérour JY, Dias N, Lansiaux A, Bailly C, Lozach O, Meijer L..  (2006)  Synthesis and biological evaluation of novel phenylcarbazoles as potential anticancer agents.,  49  (2): [PMID:16420063] [10.1021/jm050945x]

3. Tao M, Park CH, Bihovsky R, Wells GJ, Husten J, Ator MA, Hudkins RL..  (2006)  Synthesis and structure-activity relationships of novel poly(ADP-ribose) polymerase-1 inhibitors.,  16  (4): [PMID:16290935] [10.1016/j.bmcl.2005.10.099]

4. Peifer C, Stoiber T, Unger E, Totzke F, Schächtele C, Marmé D, Brenk R, Klebe G, Schollmeyer D, Dannhardt G..  (2006)  Design, synthesis, and biological evaluation of 3,4-diarylmaleimides as angiogenesis inhibitors.,  49  (4): [PMID:16480264] [10.1021/jm0580297]

Source

Source(1):

• Scientific Literature